Patent GB-1210507-A (GB)
Title: A process for the preparation of new biologically active substituted s-triazines
Inventor: HEIMBERGER WERNER
IPC: C07D251/70
Filed: 1967-11-24
Abstract: 1,210,507. s-Triazines. DEUTSCHE GOLDUND SILBER-SCHEIDEANSTALT. 24 Nov., 1967 [24 Nov., 1966], No. 53684/67. Heading C2C. Novel antiphlogistic compounds (including salts thereof) of the general formula in which X represents a cycloalkyldiimine radical attached through a nitrogen atom, e.g. piperazine or homopiperazine, or their N<SP>1</SP>-alkyl-, N<SP>1</SP>-alkylol- or N<SP>1</SP>-acyl-substitution products in which the alkyl- or the alkylol-groups contain from 1 to 6 carbons and the acyl radical represents -COOAlk, -COAlk, -COAlkylene- OAlk or -COAlkylene-O-phenyl (Alk and Alkylene contain from 1 to 6 C and in which formula R<SP>1</SP> represents any of the radicals in which Y and Y<SP>1</SP> are the same or different and represent a hydrogen or halogen atom or -NO 2 , -Alk, -OAlk, -OH or -COOH group in which Alk signifies a C 1-6  alkyl group; and R<SP>2</SP> represents an -NR-N.R<SP>3</SP>.R<SP>4</SP>, -NR<SP>4</SP>- N=R<SP>5</SP>, or -NR<SP>6</SP>R<SP>7</SP> group or the morpholino-, piperidino-, pyrrolidino, homopiperazino or piperazino radical, in which R, R<SP>3</SP> and R<SP>4</SP> are the same or different and represent a hydrogen atom or a linear or branched alkyl group with from 1 to 6 carbon atoms or an aryl radical, R<SP>5</SP> represents a linear or branched alkylidene, cycloalkylidene or arylalkylidene radical, R<SP>6</SP> and R<SP>7</SP> are the same or different and represent a hydrogen atom or a linear or branched alkyl or hydroxyalkyl group with from 1 to 6 carbons, or an aminoalkylamino, alkylaminoalkylamino or phenylaminoalkylamino radical in which the alkyl groups contain 1 to 6 C or together with the nitrogen atom to which they are attached represent a morpholinoalkyl, piperazinylalkyl- or homo-piperazinylalkyl group, are prepared: (a) by reacting a tris-halogen-s-triazine with the appropriate (YY<SP>1</SP>)-aniline, -cyclohexylamine or α-naphthylamine, thus replacing one of the halogen atoms, followed by reaction of the resulting compound with a compound of general formula HX or HR<SP>2</SP> (from which piperazine and homopiperazine are excluded in cases where it is only intended to produce monopiperazine or monohomopiperazine compounds) and the resulting compound is further reacted with piperazine or homopiperazine; (b) by reacting the tris-halogen-s-triazine first with the compound of general formula HX or HR<SP>2</SP> then with the appropriate aforementioned (YY<SP>1</SP>)- amine and then with piperazine or homopiperazine; (c) by reacting a monohalogen-R<SP>1</SP>,R<SP>2</SP>- triazine or monohalogen-R<SP>1</SP>, X-triazine (R<SP>2</SP> and X as previously defined with the exception that they are not piperazine or homopiperazine radicals in cases where it is only intended to produce monopiperazine or monohomopiperazine compounds) with piperazine or homopiperazine; or (d) a dihalogen-A-, monohalogen - A,R<SP>2</SP> - or monohalogen - A,X - substituted-triazine in which A represents the groups -SH, -SAlk, -OAlk or -O-phenyl is reacted by any of the methods (a), (b) and (c) except that in this case the piperazine or homopiperazine radical may also be introduced in the second step. Optional acylation of compounds containing the cycloalkyldiimine radical may also be effected. 2 - Morpholino - 4,6 - dichloro - s - triazine, obtained by the interaction of cyanuric chloride and morpholine, is converted to 2-morpholino-4- anilino - 6 - chloro - s triazine by reaction with aniline (2 - anilino - 4,6 - dichloro - s - triazine, obtained by the interaction of aniline and cyanuric chloride, is also converted to the foregoing morpholino compound utilizing morpholine) ; 2 - (3 - nitro - anilino) -, 2 - (2 -, 3 - and 4 - methyl - anilino) -, 2 - (2 - methoxy - 4 - chloroanilino) -, 2 - (4 - methoxy - anilino) -, 2 - (4- hydroxy - anilino) - and 2 - (α) - naphthylamino- 4 - morpholino - 6 - chloro - s - triazine are similarly obtained.